Save this story Save Story Save this story It’s the best time of the year: GQ ’s annual Men of the Year Party. For three-plus decades and counting, November in Los Angeles has been punctuated by the starriest, most show-stopping event of the season. (Actually, there have been a few exceptions—like MOTY 2002, which honored that year’s magazine cover stars Denzel Washington, Hugh Grant, and Ralph Lauren—that took place in New York City. As an event, it’s sort of spiritually bicoastal.) And when we’re talking about the biggest menswear red carpet of the year, let’s just say that “big menswear” has meant a lot of different things through the high-octane 1990s, the freaky-deaky early aughts, the buttoned-up 2010s, and the no-rules 2020s.
With the latest iteration of the Men of the Year bash just around the corner, we’re taking a look back at a smattering of the biggest, boldest looks to ever strut the MOTY red carpet, from OutKast ’s galactic-level fits in ’02 to Dwayne Johnson ’s take on the post-WWE modern cowboy in 2024.
Which burgeoning style icons will earn their rightful place in this hall of fame this year? Keep a close eye on GQ.com this month to find out.
Expand Evan Agostini / Getty Images 1/73 Lenny Kravitz, 1999 🎶 I want to get away / I want to flyyy awayyyy 🎶
Expand Gilbert Flores/Getty Images 2/73 Megan Thee Stallion, 2023 Absolutely.
Expand Mark Mainz / Getty Images 3/73 Adrien Brody, 2003 Would you look at that swoop of hair!
Expand Michael Buckner/Getty Images 4/73 Oscar Isaac, 2025 Was Oscar Isaac born to wear this Tom Ford suit? Scientists want to know.
Expand Jon Kopaloff / Getty Images 5/73 Robert Pattinson, 2017 Remember the air tie? Those were the good days.
Expand Ron Galella / Getty Images 6/73 Beyoncé, 2003 MOTY is all about pulling up in style.
Expand Axelle/Bauer-Griffin 7/73 Shaboozey, 2024 The first and only “Man of the Year” sash we've ever seen on the MOTY carpet.
Expand Rodin Eckenroth / Getty Images 8/73 Tom Holland, 2021 Sheesh!
Expand Amy Sussman/Getty Images 9/73 Hailey Bieber, 2025 The Gucci dress seen ’round the world.
Expand Steve Eichner / Getty Images 10/73 Steven Spielberg and Gwyneth Paltrow, 1999 There's nothing wrong with re-wearing your Oscars tux.
Expand Gilbert Flores/Getty Images 11/73 Jacob Elordi, 2023 From now on, let's refer to the color combo of this custom Bottega Veneta suit as “charcoal lemonade.”
Expand Jon Kopaloff / Getty Images 12/73 Snoop Dogg, 2017 Nothing can touch Snoop's elegance.
Expand Phillip Faraone / Getty Images 13/73 Troye Sivan, 2021 Business on top, “Rush” on bottom.
Expand Lester Cohen / Getty Images 14/73 Rihanna, 2012 Has Rihanna ever not been in her bad-gal era?
Expand Ron Galella / Getty Images 15/73 Jennifer Lopez, 1998 Tweed has never looked this slinky since.
Expand Leon Bennett / Getty Images 16/73 Quavo, 2021 Mixed greens.
Expand Patrick McMullan / Getty Images 17/73 Omarion, 2010 With a Louis Vuitton-monogrammed fur sash under the suit jacket? There are levels to this.
Expand Frazer Harrison/Getty Images 18/73 Kim Kardashian, 2023 Nothing screams GQ more than the phrase “custom Chrome Hearts.”
Expand Ron Galella / Getty Images 19/73 Iman, 1997 The one and only Iman, looking élégante as always.
Expand Michael Buckner / Getty Images 20/73 Leonardo DiCaprio, 2008 A nice velvet suit moment from Leo.
Expand Axelle/Bauer-Griffin 21/73 Dwayne Johnson, 2024 Yeehaw!
Expand Stefanie Keenan / Getty Images 22/73 Julia Fox, 2019 Hot on the heels of Uncut Gems , Julia Fox had arrived.
Expand Kevin Winter / Getty Images 23/73 Usher, 2004 All hail the king .
Expand Jim Spellman / Getty Images 24/73 Andrew Lauren, Ralph Lauren, Ricky Lauren, Dylan Lauren and David Lauren, 2002 A true-blue American dynasty.
Expand Frazer Harrison/Getty Images 25/73 Tom Ford, 2023 The one, the only.
Expand Michael Buckner / Getty Images 26/73 Zac Efron, 2008 He had his head in the game with this all-black ensemble.
Expand Carmen Valdes / Getty Images 27/73 OutKast, 2002 Gold quilted trousers, oversized prom-king tux, can't lose.
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Source: Celebrities
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